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I think you have to finish the werewolf event first, or you just have to go on the hunting trip with him on Friday (around 18-20 I believe, it should say what time in a dialogue with him), and sleep on the bed with him, after that it should increase your love with him and you'll be able to trigger a sex scene with him by going to his house at night

encouraged Logan I don't believe can go further, Bernard you can have i think 3 if you count the werewolf scenes when he isn't completely there. 4 or more if you count the werewolf boss as well. The ones where he is conscious are, the date night scene that has a couple routes depending on which position you prefer and if you have seen his transformation at the cottage (which only counts after you get the sex scene once), the one with Caleb when you get Bernard to four hearts and Caleb to 1 and the love potion is all for him,

You can get Encouraged Logan's likeness higher than 10, but it doesn't really make a difference anyway I think. I have him at 27 in my Encouraged route with him, though he still has the same attitude on me as he was on lower likeness. Nonetheless, at least I get to see him get fucked a lot lol.